Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804002685/cv6269sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804002685/cv6269Isup2.hkl |
CCDC reference: 236026
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.005 Å
- R factor = 0.034
- wR factor = 0.087
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.34 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.46 Ratio
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.21 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C15
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 3497 Count of symmetry unique reflns 1845 Completeness (_total/calc) 189.54% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1652 Fraction of Friedel pairs measured 0.895 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001).
[Fe(C5H5)(C12H14NO3)] | Dx = 1.477 Mg m−3 |
Mr = 341.18 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43 | Cell parameters from 1852 reflections |
Hall symbol: P 4cw | θ = 1.0–27.5° |
a = 11.4599 (2) Å | µ = 0.99 mm−1 |
c = 11.6864 (2) Å | T = 150 K |
V = 1534.77 (5) Å3 | Prism, brown |
Z = 4 | 0.52 × 0.40 × 0.28 mm |
F(000) = 712 |
Nonius KappaCCD diffractometer | 3497 independent reflections |
Radiation source: fine-focus sealed tube | 3323 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.044 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω and φ scans to fill the Ewald sphere | h = −14→14 |
Absorption correction: multi-scan (SORTAV; Blessing 1997) | k = −14→14 |
Tmin = 0.681, Tmax = 0.757 | l = −14→15 |
27433 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.8632P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3497 reflections | Δρmax = 0.71 e Å−3 |
205 parameters | Δρmin = −0.32 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.020 (17) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ————————————————————– Least-Squares Planes - P*X+Q*Y+R*Z=S ————————————————————– Nr 1 P Q R S ————————————————————– oxazo -.1653 (13). 9720 (4) -.1670 (15) 8.993 (8) perpendicular distances of the defining atoms to the l.s.-plane O(3). 061 (2) N -.040 (2) C(12) -.014 (2) C(13). 070 (3) C(14) -.078 (3) ————————————————————– Nr 2 P Q R S ————————————————————– Cp1 -.0450 (14). 9925 (2) -.1134 (15) 9.752 (11) perpendicular distances of the defining atoms to the l.s.-plane C(1) -.001 (2) C(2) -.002 (2) C(3). 001 (2) C(4) -.002 (3) C(5). 000 (3) ————————————————————– Nr 3 P Q R S ————————————————————– Cp2 -.0472 (14). 9953 (1) -.0850 (15) 6.636 (11) perpendicular distances of the defining atoms to the l.s.-plane C(6). 001 (2) C(7). 002 (2) C(8) -.001 (2) C(9). 002 (3) C(10) -.001 (3) ————————————————————– Nr 4 P Q R S ————————————————————– COO -.022 (4). 9964 (1) -.0818 (18) 10.03 (2) perpendicular distances of the defining atoms to the l.s.-plane O(1) -.001 (2) O(2) -.001 (2) C(11) -.001 (2) ————————————————————– Dihedral angles of the l.s.-planes 1,2 = 7.65 (17) 1,3 = 8.35 (17) 1,4 = 9.7 (3) 2,3 = 1.64 (17) 2,4 = 2.3 (3) 3,4 = 1.5 (3) ————————————————————– |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Fe | 0.27611 (3) | 0.78048 (3) | 0.46928 (3) | 0.02614 (10) | |
N | 0.3220 (2) | 0.8863 (2) | 0.15844 (19) | 0.0327 (5) | |
O1 | 0.56936 (17) | 0.9282 (2) | 0.4460 (2) | 0.0440 (5) | |
O2 | 0.51445 (17) | 0.91199 (19) | 0.26653 (19) | 0.0378 (4) | |
O3 | 0.13067 (16) | 0.86941 (16) | 0.19636 (16) | 0.0322 (4) | |
C1 | 0.3664 (2) | 0.9224 (2) | 0.4157 (2) | 0.0293 (5) | |
C2 | 0.2577 (2) | 0.9102 (2) | 0.3544 (2) | 0.0267 (5) | |
C3 | 0.1646 (2) | 0.9157 (2) | 0.4355 (3) | 0.0329 (6) | |
H3 | 0.0854 | 0.9105 | 0.4191 | 0.039* | |
C4 | 0.2151 (3) | 0.9306 (3) | 0.5463 (3) | 0.0374 (6) | |
H4 | 0.1742 | 0.9364 | 0.6147 | 0.045* | |
C5 | 0.3380 (3) | 0.9350 (3) | 0.5344 (3) | 0.0369 (6) | |
H5 | 0.3913 | 0.9444 | 0.5937 | 0.044* | |
C6 | 0.3815 (2) | 0.6389 (2) | 0.4473 (3) | 0.0371 (7) | |
H6 | 0.4580 | 0.6403 | 0.4207 | 0.045* | |
C7 | 0.2805 (3) | 0.6282 (2) | 0.3784 (3) | 0.0340 (6) | |
H7 | 0.2788 | 0.6214 | 0.2992 | 0.041* | |
C8 | 0.1818 (2) | 0.6297 (2) | 0.4525 (3) | 0.0364 (6) | |
H8 | 0.1041 | 0.6238 | 0.4301 | 0.044* | |
C9 | 0.2228 (2) | 0.6419 (3) | 0.5663 (3) | 0.0378 (6) | |
H9 | 0.1768 | 0.6458 | 0.6318 | 0.045* | |
C10 | 0.3470 (2) | 0.6472 (3) | 0.5628 (3) | 0.0368 (6) | |
H10 | 0.3964 | 0.6547 | 0.6254 | 0.044* | |
C11 | 0.4911 (2) | 0.9207 (2) | 0.3766 (2) | 0.0309 (5) | |
C12 | 0.2410 (2) | 0.88777 (19) | 0.2324 (2) | 0.0271 (5) | |
C13 | 0.2686 (3) | 0.8672 (3) | 0.0449 (3) | 0.0387 (6) | |
H13 | 0.2678 | 0.9428 | 0.0057 | 0.046* | |
C14 | 0.1415 (3) | 0.8375 (3) | 0.0747 (2) | 0.0369 (6) | |
H14A | 0.0878 | 0.8825 | 0.0280 | 0.044* | |
H14B | 0.1261 | 0.7551 | 0.0634 | 0.044* | |
C15 | 0.3415 (3) | 0.7844 (3) | −0.0284 (4) | 0.0561 (8) | |
H15 | 0.4165 | 0.8218 | −0.0449 | 0.067* | |
C16 | 0.3641 (4) | 0.6706 (4) | 0.0296 (4) | 0.0666 (11) | |
H16A | 0.2913 | 0.6321 | 0.0446 | 0.100* | |
H16B | 0.4042 | 0.6843 | 0.1005 | 0.100* | |
H16C | 0.4115 | 0.6224 | −0.0189 | 0.100* | |
C17 | 0.2788 (6) | 0.7613 (7) | −0.1415 (5) | 0.116 (3) | |
H17A | 0.3312 | 0.7232 | −0.1936 | 0.174* | |
H17B | 0.2535 | 0.8340 | −0.1740 | 0.174* | |
H17C | 0.2124 | 0.7122 | −0.1281 | 0.174* | |
H90 | 0.450 (5) | 0.905 (5) | 0.211 (6) | 0.107 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe | 0.02504 (17) | 0.02835 (18) | 0.02503 (16) | −0.00284 (14) | −0.00033 (15) | −0.00254 (15) |
N | 0.0330 (11) | 0.0366 (12) | 0.0285 (12) | 0.0015 (9) | −0.0041 (9) | −0.0003 (9) |
O1 | 0.0311 (10) | 0.0543 (12) | 0.0466 (13) | −0.0079 (9) | −0.0107 (9) | 0.0023 (10) |
O2 | 0.0277 (9) | 0.0472 (11) | 0.0385 (10) | 0.0040 (8) | 0.0017 (8) | 0.0037 (9) |
O3 | 0.0307 (9) | 0.0336 (9) | 0.0321 (10) | −0.0042 (7) | −0.0071 (7) | 0.0012 (8) |
C1 | 0.0296 (12) | 0.0258 (12) | 0.0324 (13) | −0.0046 (10) | −0.0019 (10) | −0.0040 (10) |
C2 | 0.0259 (12) | 0.0236 (11) | 0.0307 (13) | 0.0003 (9) | −0.0010 (10) | −0.0017 (10) |
C3 | 0.0279 (12) | 0.0302 (12) | 0.0406 (15) | 0.0018 (10) | 0.0029 (10) | −0.0073 (10) |
C4 | 0.0383 (15) | 0.0393 (15) | 0.0347 (14) | 0.0004 (11) | 0.0045 (12) | −0.0123 (12) |
C5 | 0.0413 (15) | 0.0357 (14) | 0.0337 (14) | −0.0041 (12) | −0.0036 (12) | −0.0105 (11) |
C6 | 0.0305 (13) | 0.0301 (12) | 0.0508 (19) | 0.0008 (10) | 0.0051 (12) | −0.0011 (12) |
C7 | 0.0417 (15) | 0.0228 (12) | 0.0376 (15) | −0.0016 (11) | −0.0021 (12) | −0.0070 (11) |
C8 | 0.0284 (12) | 0.0305 (12) | 0.0502 (18) | −0.0078 (10) | −0.0099 (12) | 0.0056 (12) |
C9 | 0.0330 (14) | 0.0418 (15) | 0.0386 (16) | −0.0040 (11) | 0.0001 (12) | 0.0113 (13) |
C10 | 0.0292 (13) | 0.0412 (15) | 0.0399 (16) | 0.0002 (11) | −0.0082 (12) | 0.0106 (12) |
C11 | 0.0279 (12) | 0.0246 (12) | 0.0403 (15) | −0.0030 (9) | −0.0025 (11) | 0.0023 (10) |
C12 | 0.0295 (11) | 0.0201 (10) | 0.0318 (13) | 0.0000 (8) | −0.0010 (10) | 0.0017 (10) |
C13 | 0.0435 (15) | 0.0457 (16) | 0.0269 (13) | 0.0049 (12) | −0.0088 (12) | −0.0010 (12) |
C14 | 0.0451 (16) | 0.0380 (14) | 0.0277 (14) | −0.0084 (12) | −0.0089 (12) | 0.0003 (11) |
C15 | 0.062 (2) | 0.064 (2) | 0.0431 (17) | 0.0021 (17) | −0.004 (2) | −0.0102 (17) |
C16 | 0.077 (3) | 0.054 (2) | 0.070 (3) | −0.0010 (19) | 0.004 (2) | −0.0123 (19) |
C17 | 0.118 (5) | 0.184 (7) | 0.047 (3) | 0.056 (5) | −0.028 (3) | −0.055 (4) |
Fe—C2 | 2.014 (3) | C5—H5 | 0.9300 |
Fe—C1 | 2.027 (3) | C6—C10 | 1.409 (5) |
Fe—C6 | 2.039 (3) | C6—C7 | 1.415 (4) |
Fe—C7 | 2.043 (3) | C6—H6 | 0.9300 |
Fe—C9 | 2.045 (3) | C7—C8 | 1.425 (4) |
Fe—C10 | 2.046 (3) | C7—H7 | 0.9300 |
Fe—C3 | 2.047 (3) | C8—C9 | 1.418 (4) |
Fe—C8 | 2.047 (3) | C8—H8 | 0.9300 |
Fe—C5 | 2.053 (3) | C9—C10 | 1.425 (4) |
Fe—C4 | 2.063 (3) | C9—H9 | 0.9300 |
N—C12 | 1.269 (3) | C10—H10 | 0.9300 |
N—C13 | 1.477 (4) | C13—C15 | 1.527 (5) |
O1—C11 | 1.213 (3) | C13—C14 | 1.536 (4) |
O2—C11 | 1.317 (4) | C13—H13 | 0.9800 |
O2—H90 | 0.98 (7) | C14—H14A | 0.9700 |
O3—C12 | 1.349 (3) | C14—H14B | 0.9700 |
O3—C14 | 1.473 (3) | C15—C16 | 1.493 (6) |
C1—C5 | 1.433 (4) | C15—C17 | 1.528 (6) |
C1—C2 | 1.444 (4) | C15—H15 | 0.9800 |
C1—C11 | 1.500 (4) | C16—H16A | 0.9600 |
C2—C3 | 1.428 (4) | C16—H16B | 0.9600 |
C2—C12 | 1.461 (4) | C16—H16C | 0.9600 |
C3—C4 | 1.428 (4) | C17—H17A | 0.9600 |
C3—H3 | 0.9300 | C17—H17B | 0.9600 |
C4—C5 | 1.416 (4) | C17—H17C | 0.9600 |
C4—H4 | 0.9300 | ||
C2—Fe—C1 | 41.87 (10) | C4—C5—C1 | 108.5 (3) |
C2—Fe—C6 | 124.42 (12) | C4—C5—Fe | 70.25 (16) |
C1—Fe—C6 | 107.27 (11) | C1—C5—Fe | 68.46 (16) |
C2—Fe—C7 | 106.64 (11) | C4—C5—H5 | 125.8 |
C1—Fe—C7 | 120.81 (11) | C1—C5—H5 | 125.8 |
C6—Fe—C7 | 40.58 (12) | Fe—C5—H5 | 127.1 |
C2—Fe—C9 | 155.72 (11) | C10—C6—C7 | 108.7 (3) |
C1—Fe—C9 | 161.28 (11) | C10—C6—Fe | 70.09 (16) |
C6—Fe—C9 | 68.23 (12) | C7—C6—Fe | 69.88 (15) |
C7—Fe—C9 | 68.43 (12) | C10—C6—H6 | 125.7 |
C2—Fe—C10 | 161.54 (11) | C7—C6—H6 | 125.7 |
C1—Fe—C10 | 124.16 (11) | Fe—C6—H6 | 125.9 |
C6—Fe—C10 | 40.37 (13) | C6—C7—C8 | 107.7 (3) |
C7—Fe—C10 | 68.29 (13) | C6—C7—Fe | 69.54 (15) |
C9—Fe—C10 | 40.77 (11) | C8—C7—Fe | 69.78 (15) |
C2—Fe—C3 | 41.17 (11) | C6—C7—H7 | 126.2 |
C1—Fe—C3 | 69.61 (11) | C8—C7—H7 | 126.2 |
C6—Fe—C3 | 161.42 (12) | Fe—C7—H7 | 126.1 |
C7—Fe—C3 | 124.17 (12) | C9—C8—C7 | 107.9 (2) |
C9—Fe—C3 | 120.56 (12) | C9—C8—Fe | 69.62 (16) |
C10—Fe—C3 | 156.34 (12) | C7—C8—Fe | 69.45 (14) |
C2—Fe—C8 | 120.23 (11) | C9—C8—H8 | 126.0 |
C1—Fe—C8 | 156.50 (12) | C7—C8—H8 | 126.0 |
C6—Fe—C8 | 68.26 (11) | Fe—C8—H8 | 126.5 |
C7—Fe—C8 | 40.76 (12) | C8—C9—C10 | 107.9 (3) |
C9—Fe—C8 | 40.55 (12) | C8—C9—Fe | 69.83 (16) |
C10—Fe—C8 | 68.33 (11) | C10—C9—Fe | 69.66 (16) |
C3—Fe—C8 | 106.89 (11) | C8—C9—H9 | 126.0 |
C2—Fe—C5 | 69.34 (11) | C10—C9—H9 | 126.0 |
C1—Fe—C5 | 41.10 (11) | Fe—C9—H9 | 126.1 |
C6—Fe—C5 | 121.86 (12) | C6—C10—C9 | 107.8 (3) |
C7—Fe—C5 | 156.99 (12) | C6—C10—Fe | 69.54 (16) |
C9—Fe—C5 | 124.54 (13) | C9—C10—Fe | 69.57 (16) |
C10—Fe—C5 | 107.97 (13) | C6—C10—H10 | 126.1 |
C3—Fe—C5 | 68.56 (12) | C9—C10—H10 | 126.1 |
C8—Fe—C5 | 160.97 (13) | Fe—C10—H10 | 126.4 |
C2—Fe—C4 | 68.89 (12) | O1—C11—O2 | 120.6 (3) |
C1—Fe—C4 | 68.82 (12) | O1—C11—C1 | 120.0 (3) |
C6—Fe—C4 | 156.78 (12) | O2—C11—C1 | 119.5 (2) |
C7—Fe—C4 | 161.25 (11) | N—C12—O3 | 118.1 (2) |
C9—Fe—C4 | 107.72 (13) | N—C12—C2 | 124.8 (2) |
C10—Fe—C4 | 121.61 (14) | O3—C12—C2 | 117.0 (2) |
C3—Fe—C4 | 40.66 (12) | N—C13—C15 | 111.7 (3) |
C8—Fe—C4 | 124.50 (12) | N—C13—C14 | 102.9 (2) |
C5—Fe—C4 | 40.23 (12) | C15—C13—C14 | 120.6 (3) |
C12—N—C13 | 108.1 (2) | N—C13—H13 | 107.0 |
C11—O2—H90 | 120 (4) | C15—C13—H13 | 107.0 |
C12—O3—C14 | 105.1 (2) | C14—C13—H13 | 107.0 |
C5—C1—C2 | 107.1 (2) | O3—C14—C13 | 104.1 (2) |
C5—C1—C11 | 120.8 (2) | O3—C14—H14A | 110.9 |
C2—C1—C11 | 132.0 (2) | C13—C14—H14A | 110.9 |
C5—C1—Fe | 70.44 (17) | O3—C14—H14B | 110.9 |
C2—C1—Fe | 68.59 (14) | C13—C14—H14B | 110.9 |
C11—C1—Fe | 124.74 (18) | H14A—C14—H14B | 109.0 |
C3—C2—C1 | 108.1 (2) | C16—C15—C13 | 112.5 (4) |
C3—C2—C12 | 123.9 (2) | C16—C15—C17 | 108.9 (4) |
C1—C2—C12 | 127.9 (2) | C13—C15—C17 | 109.6 (3) |
C3—C2—Fe | 70.63 (16) | C16—C15—H15 | 108.6 |
C1—C2—Fe | 69.54 (15) | C13—C15—H15 | 108.6 |
C12—C2—Fe | 122.30 (17) | C17—C15—H15 | 108.6 |
C4—C3—C2 | 107.7 (2) | C15—C16—H16A | 109.5 |
C4—C3—Fe | 70.29 (16) | C15—C16—H16B | 109.5 |
C2—C3—Fe | 68.20 (15) | H16A—C16—H16B | 109.5 |
C4—C3—H3 | 126.1 | C15—C16—H16C | 109.5 |
C2—C3—H3 | 126.1 | H16A—C16—H16C | 109.5 |
Fe—C3—H3 | 126.9 | H16B—C16—H16C | 109.5 |
C5—C4—C3 | 108.6 (3) | C15—C17—H17A | 109.5 |
C5—C4—Fe | 69.51 (16) | C15—C17—H17B | 109.5 |
C3—C4—Fe | 69.05 (16) | H17A—C17—H17B | 109.5 |
C5—C4—H4 | 125.7 | C15—C17—H17C | 109.5 |
C3—C4—H4 | 125.7 | H17A—C17—H17C | 109.5 |
Fe—C4—H4 | 127.3 | H17B—C17—H17C | 109.5 |
C2—Fe—C1—C5 | 118.3 (2) | C4—Fe—C5—C1 | −120.3 (3) |
C6—Fe—C1—C5 | −118.98 (18) | C2—Fe—C6—C10 | 165.75 (16) |
C7—Fe—C1—C5 | −161.20 (17) | C1—Fe—C6—C10 | 122.82 (17) |
C9—Fe—C1—C5 | −46.0 (4) | C7—Fe—C6—C10 | −119.7 (2) |
C10—Fe—C1—C5 | −77.8 (2) | C9—Fe—C6—C10 | −37.88 (17) |
C3—Fe—C1—C5 | 80.38 (18) | C3—Fe—C6—C10 | −159.9 (3) |
C8—Fe—C1—C5 | 166.0 (2) | C8—Fe—C6—C10 | −81.69 (18) |
C4—Fe—C1—C5 | 36.75 (18) | C5—Fe—C6—C10 | 80.2 (2) |
C6—Fe—C1—C2 | 122.68 (16) | C4—Fe—C6—C10 | 46.4 (4) |
C7—Fe—C1—C2 | 80.46 (18) | C2—Fe—C6—C7 | −74.6 (2) |
C9—Fe—C1—C2 | −164.3 (3) | C1—Fe—C6—C7 | −117.48 (17) |
C10—Fe—C1—C2 | 163.81 (16) | C9—Fe—C6—C7 | 81.82 (18) |
C3—Fe—C1—C2 | −37.96 (15) | C10—Fe—C6—C7 | 119.7 (2) |
C8—Fe—C1—C2 | 47.6 (3) | C3—Fe—C6—C7 | −40.2 (4) |
C5—Fe—C1—C2 | −118.3 (2) | C8—Fe—C6—C7 | 38.01 (18) |
C4—Fe—C1—C2 | −81.58 (17) | C5—Fe—C6—C7 | −160.10 (17) |
C2—Fe—C1—C11 | −127.1 (3) | C4—Fe—C6—C7 | 166.1 (3) |
C6—Fe—C1—C11 | −4.4 (3) | C10—C6—C7—C8 | −0.1 (3) |
C7—Fe—C1—C11 | −46.7 (3) | Fe—C6—C7—C8 | −59.62 (18) |
C9—Fe—C1—C11 | 68.6 (5) | C10—C6—C7—Fe | 59.6 (2) |
C10—Fe—C1—C11 | 36.7 (3) | C2—Fe—C7—C6 | 123.91 (18) |
C3—Fe—C1—C11 | −165.1 (3) | C1—Fe—C7—C6 | 80.5 (2) |
C8—Fe—C1—C11 | −79.5 (4) | C9—Fe—C7—C6 | −81.29 (18) |
C5—Fe—C1—C11 | 114.5 (3) | C10—Fe—C7—C6 | −37.27 (18) |
C4—Fe—C1—C11 | 151.3 (3) | C3—Fe—C7—C6 | 165.61 (17) |
C5—C1—C2—C3 | 0.2 (3) | C8—Fe—C7—C6 | −118.8 (2) |
C11—C1—C2—C3 | 178.5 (3) | C5—Fe—C7—C6 | 47.7 (4) |
Fe—C1—C2—C3 | 60.37 (18) | C4—Fe—C7—C6 | −162.9 (4) |
C5—C1—C2—C12 | −175.8 (2) | C2—Fe—C7—C8 | −117.26 (17) |
C11—C1—C2—C12 | 2.5 (4) | C1—Fe—C7—C8 | −160.65 (16) |
Fe—C1—C2—C12 | −115.6 (3) | C6—Fe—C7—C8 | 118.8 (2) |
C5—C1—C2—Fe | −60.2 (2) | C9—Fe—C7—C8 | 37.55 (17) |
C11—C1—C2—Fe | 118.1 (3) | C10—Fe—C7—C8 | 81.56 (18) |
C1—Fe—C2—C3 | −118.9 (2) | C3—Fe—C7—C8 | −75.6 (2) |
C6—Fe—C2—C3 | 164.15 (16) | C5—Fe—C7—C8 | 166.5 (3) |
C7—Fe—C2—C3 | 123.27 (16) | C4—Fe—C7—C8 | −44.0 (5) |
C9—Fe—C2—C3 | 49.0 (3) | C6—C7—C8—C9 | 0.3 (3) |
C10—Fe—C2—C3 | −165.6 (3) | Fe—C7—C8—C9 | −59.20 (19) |
C8—Fe—C2—C3 | 81.07 (19) | C6—C7—C8—Fe | 59.47 (18) |
C5—Fe—C2—C3 | −80.67 (17) | C2—Fe—C8—C9 | −160.35 (17) |
C4—Fe—C2—C3 | −37.47 (16) | C1—Fe—C8—C9 | 164.9 (2) |
C6—Fe—C2—C1 | −76.99 (18) | C6—Fe—C8—C9 | 81.49 (19) |
C7—Fe—C2—C1 | −117.86 (16) | C7—Fe—C8—C9 | 119.3 (2) |
C9—Fe—C2—C1 | 167.8 (3) | C10—Fe—C8—C9 | 37.88 (18) |
C10—Fe—C2—C1 | −46.7 (4) | C3—Fe—C8—C9 | −117.53 (18) |
C3—Fe—C2—C1 | 118.9 (2) | C5—Fe—C8—C9 | −44.4 (4) |
C8—Fe—C2—C1 | −160.07 (15) | C4—Fe—C8—C9 | −76.4 (2) |
C5—Fe—C2—C1 | 38.20 (16) | C2—Fe—C8—C7 | 80.32 (19) |
C4—Fe—C2—C1 | 81.40 (17) | C1—Fe—C8—C7 | 45.5 (3) |
C1—Fe—C2—C12 | 122.6 (3) | C6—Fe—C8—C7 | −37.84 (18) |
C6—Fe—C2—C12 | 45.7 (3) | C9—Fe—C8—C7 | −119.3 (2) |
C7—Fe—C2—C12 | 4.8 (2) | C10—Fe—C8—C7 | −81.45 (19) |
C9—Fe—C2—C12 | −69.5 (4) | C3—Fe—C8—C7 | 123.14 (18) |
C10—Fe—C2—C12 | 75.9 (4) | C5—Fe—C8—C7 | −163.8 (3) |
C3—Fe—C2—C12 | −118.5 (3) | C4—Fe—C8—C7 | 164.27 (18) |
C8—Fe—C2—C12 | −37.4 (3) | C7—C8—C9—C10 | −0.4 (3) |
C5—Fe—C2—C12 | 160.8 (2) | Fe—C8—C9—C10 | −59.5 (2) |
C4—Fe—C2—C12 | −156.0 (2) | C7—C8—C9—Fe | 59.09 (18) |
C1—C2—C3—C4 | −0.3 (3) | C2—Fe—C9—C8 | 44.9 (4) |
C12—C2—C3—C4 | 175.9 (2) | C1—Fe—C9—C8 | −161.1 (3) |
Fe—C2—C3—C4 | 59.4 (2) | C6—Fe—C9—C8 | −81.56 (19) |
C1—C2—C3—Fe | −59.68 (18) | C7—Fe—C9—C8 | −37.74 (18) |
C12—C2—C3—Fe | 116.5 (2) | C10—Fe—C9—C8 | −119.1 (3) |
C2—Fe—C3—C4 | −119.4 (2) | C3—Fe—C9—C8 | 80.2 (2) |
C1—Fe—C3—C4 | −80.86 (18) | C5—Fe—C9—C8 | 163.91 (17) |
C6—Fe—C3—C4 | −164.5 (3) | C4—Fe—C9—C8 | 122.76 (18) |
C7—Fe—C3—C4 | 165.06 (17) | C2—Fe—C9—C10 | 164.0 (3) |
C9—Fe—C3—C4 | 81.7 (2) | C1—Fe—C9—C10 | −42.0 (5) |
C10—Fe—C3—C4 | 49.3 (3) | C6—Fe—C9—C10 | 37.52 (19) |
C8—Fe—C3—C4 | 123.70 (18) | C7—Fe—C9—C10 | 81.3 (2) |
C5—Fe—C3—C4 | −36.72 (17) | C3—Fe—C9—C10 | −160.76 (18) |
C1—Fe—C3—C2 | 38.58 (15) | C8—Fe—C9—C10 | 119.1 (3) |
C6—Fe—C3—C2 | −45.0 (4) | C5—Fe—C9—C10 | −77.0 (2) |
C7—Fe—C3—C2 | −75.51 (19) | C4—Fe—C9—C10 | −118.2 (2) |
C9—Fe—C3—C2 | −158.89 (16) | C7—C6—C10—C9 | −0.2 (3) |
C10—Fe—C3—C2 | 168.7 (3) | Fe—C6—C10—C9 | 59.3 (2) |
C8—Fe—C3—C2 | −116.87 (17) | C7—C6—C10—Fe | −59.43 (19) |
C5—Fe—C3—C2 | 82.71 (17) | C8—C9—C10—C6 | 0.3 (3) |
C4—Fe—C3—C2 | 119.4 (2) | Fe—C9—C10—C6 | −59.2 (2) |
C2—C3—C4—C5 | 0.3 (3) | C8—C9—C10—Fe | 59.6 (2) |
Fe—C3—C4—C5 | 58.4 (2) | C2—Fe—C10—C6 | −39.9 (4) |
C2—C3—C4—Fe | −58.09 (18) | C1—Fe—C10—C6 | −75.9 (2) |
C2—Fe—C4—C5 | −82.6 (2) | C7—Fe—C10—C6 | 37.46 (17) |
C1—Fe—C4—C5 | −37.52 (18) | C9—Fe—C10—C6 | 119.2 (3) |
C6—Fe—C4—C5 | 47.0 (4) | C3—Fe—C10—C6 | 164.2 (2) |
C7—Fe—C4—C5 | −162.1 (3) | C8—Fe—C10—C6 | 81.48 (19) |
C9—Fe—C4—C5 | 122.95 (19) | C5—Fe—C10—C6 | −118.37 (18) |
C10—Fe—C4—C5 | 80.4 (2) | C4—Fe—C10—C6 | −160.41 (17) |
C3—Fe—C4—C5 | −120.5 (3) | C2—Fe—C10—C9 | −159.1 (3) |
C8—Fe—C4—C5 | 164.51 (18) | C1—Fe—C10—C9 | 164.96 (18) |
C2—Fe—C4—C3 | 37.92 (16) | C6—Fe—C10—C9 | −119.2 (3) |
C1—Fe—C4—C3 | 82.97 (18) | C7—Fe—C10—C9 | −81.71 (19) |
C6—Fe—C4—C3 | 167.5 (3) | C3—Fe—C10—C9 | 45.0 (4) |
C7—Fe—C4—C3 | −41.6 (5) | C8—Fe—C10—C9 | −37.68 (19) |
C9—Fe—C4—C3 | −116.55 (18) | C5—Fe—C10—C9 | 122.5 (2) |
C10—Fe—C4—C3 | −159.08 (16) | C4—Fe—C10—C9 | 80.4 (2) |
C8—Fe—C4—C3 | −75.0 (2) | C5—C1—C11—O1 | 1.1 (4) |
C5—Fe—C4—C3 | 120.5 (3) | C2—C1—C11—O1 | −177.0 (3) |
C3—C4—C5—C1 | −0.2 (3) | Fe—C1—C11—O1 | −85.4 (3) |
Fe—C4—C5—C1 | 57.9 (2) | C5—C1—C11—O2 | −178.3 (3) |
C3—C4—C5—Fe | −58.1 (2) | C2—C1—C11—O2 | 3.6 (4) |
C2—C1—C5—C4 | 0.0 (3) | Fe—C1—C11—O2 | 95.2 (3) |
C11—C1—C5—C4 | −178.5 (2) | C13—N—C12—O3 | 1.9 (3) |
Fe—C1—C5—C4 | −59.0 (2) | C13—N—C12—C2 | −176.9 (2) |
C2—C1—C5—Fe | 59.03 (18) | C14—O3—C12—N | 6.8 (3) |
C11—C1—C5—Fe | −119.5 (2) | C14—O3—C12—C2 | −174.3 (2) |
C2—Fe—C5—C4 | 81.4 (2) | C3—C2—C12—N | 177.6 (3) |
C1—Fe—C5—C4 | 120.3 (3) | C1—C2—C12—N | −7.0 (4) |
C6—Fe—C5—C4 | −160.15 (18) | Fe—C2—C12—N | −95.1 (3) |
C7—Fe—C5—C4 | 165.3 (3) | C3—C2—C12—O3 | −1.2 (3) |
C9—Fe—C5—C4 | −76.0 (2) | C1—C2—C12—O3 | 174.2 (2) |
C10—Fe—C5—C4 | −118.0 (2) | Fe—C2—C12—O3 | 86.1 (2) |
C3—Fe—C5—C4 | 37.10 (19) | C12—N—C13—C15 | −140.0 (3) |
C8—Fe—C5—C4 | −42.5 (4) | C12—N—C13—C14 | −9.3 (3) |
C2—Fe—C5—C1 | −38.89 (16) | C12—O3—C14—C13 | −11.8 (3) |
C6—Fe—C5—C1 | 79.6 (2) | N—C13—C14—O3 | 12.6 (3) |
C7—Fe—C5—C1 | 45.1 (4) | C15—C13—C14—O3 | 137.7 (3) |
C9—Fe—C5—C1 | 163.72 (16) | N—C13—C15—C16 | 55.0 (4) |
C10—Fe—C5—C1 | 121.74 (18) | C14—C13—C15—C16 | −65.8 (4) |
C3—Fe—C5—C1 | −83.15 (18) | N—C13—C15—C17 | 176.3 (4) |
C8—Fe—C5—C1 | −162.7 (3) | C14—C13—C15—C17 | 55.5 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H90···N | 0.98 (7) | 1.61 (6) | 2.558 (3) | 161 (6) |
C3—H3···O3i | 0.93 | 2.54 | 3.427 (3) | 160 |
C8—H8···Ni | 0.93 | 2.58 | 3.470 (3) | 159 |
Symmetry code: (i) y−1, −x+1, z+1/4. |